From Fira To Oia, Walking the Caldera Trail in Santorini

Here's a thing that I wrote about making poor decisions and walking a long way

By Jackson Cresswell

In the morning of my second day in Santorini, I walked the trail from Fira to Oia. The coastal cliffside hike is a well-known and well publicized feature of the island. It’s often listed as one of the best things to do when visiting the island. The entire trail is filled with incredible views of the Caldera and volcano. You can also see the lower, flatter farmlands and beaches of the eastern side of the island. Sometimes the trail will offer you views of both sides of the island at once. The cities at either end of the trail, Fira and Oia, are the two most popular towns on the Caldera, known for their restaurants, bars, resorts and views of the sunset. In my opinion, the hiking trail and the towns that bookend it represent the best that Santorini has to offer and I experienced it all unintentionally.

Let me explain.

The day before I accidentally hiked to Oia was a long one, so I think I can be forgiven for not paying full attention when the details of the trail were laid out for me. I spent most of the previous 24 hours on airplanes or in terminals. I saw the sun set over the east coast of the U.S., watched it rise again over London, landed and had breakfast in Frankfurt, Germany, caught another flight to Athens where I had lunch, and finally flew into the Santorini airstrip around 5 p.m. I took a taxi to Fira and checked in to my hotel. The clerk there could not have been nicer. She laid out a map of the island and went to work with a pen, marking places I might want to visit (like Akrotiri), explaining how to get around using the buses, telling me about the best restaurants, and giving me a rundown of the island’s history. In the days that followed, I used her map as my unofficial guidebook. However, in that moment, I was exhausted, jet lagged, and excited to be in a new place. In other words, I was distracted. So when she mentioned the trail, I didn’t fully absorb the details. I dropped off my bags, had dinner in town, and returned to my hotel to watch the second sunset of my day, from the second continent of my day.

The next morning, after breakfast, I walked into Fira to familiarize myself with the town. I started by weaving between the different shops, pubs and cafes, making my way south. When I hit the edge of the town, near the hospital, I turned around and made my way back. When I got back to the hotel, I decided to keep walking north along the cliffs toward the cable car. I was taking my time, stopping to take photos not only for the views of the town, but also to leave myself a sort of trail of breadcrumbs in case my sense of direction let me down. I also took a picture of the map and the bus schedule the night before just to have them with me if I needed them. At least if I got lost, I’d be able to pass the time by looking through my albums while waiting to be rescued. When I made it to the cable car, I looked back down the hill at Fira and took a photo. The Caldera is crescent shaped and Fira is more or less situated in the middle of the curve. As you move north, the elevation goes up and the trail moves out from the town. So, essentially, the farther north you go, the more of the city you can see and the better the view becomes. In my attempt to take better and better photos, I continued to move north toward Firostefani. Because of some construction work and related donkey traffic on the trail, I detoured into the town. I kept going north, but took time to look around Firostefani. I continued pausing every once in a while to take pictures of landmarks or street signs. I was still leaving breadcrumbs.

Here’s the trick I kept playing on myself that eventually led me to end up in Oia. I kept reasoning, perhaps unwisely, that if I could see the next town, I could walk there. And if I could walk there, I could eventually walk back. In reality the trail is about 12 kilometers long and takes an average of about 4 hours to complete one way.

Thankfully, I was wearing comfortable shoes, because much of the walk that followed seemed to be uphill.

I eventually got back to the cliffside path near the northern edge of Firostefani. I bought a soda in town, so I was taking in caffeine as I walked and keeping my energy up so when I looked back and saw Fira behind me and the town of Imerovigli just up the hill, I thought to myself that I hadn’t actually gone that far from the hotel. I figured I could probably walk back in no time. I checked the map on my phone, and the distance looked so small on the screen that I decided to keep going. I’d been walking around for more than an hour, but I’d been stopping to take pictures so it wasn’t like I was an hour from the hotel.

I walked to Imerovigli. More pictures. More caffeine.

Imerovigli is in many ways the point of no return for the hike. If you look at a map of Santorini, you’ll notice that the portion from Fira to Imerovigli is only about a third of the total trail, so there’s still a long way to go. It’s also the last real town before you get Finikia, so if you need any snacks, drinks, bathrooms or wi-fi access, that’s the place to get your fill. It’s also the last time you’ll see Fira for a while, because as the coastline breaks back to the east, the island bottlenecks and the hills obscure your view of Fira, replacing it with mostly empty ridgelines that roll down into farmland on the east and steep cliffs on the west.

The trail past Imerovigli is well worn and easy to follow. Yet despite that, I still managed to wander through a fence onto what I assume was actually someone’s private land. I figured it out pretty quickly and got back on track, but it’s probably a good idea to avoid doing that whenever possible. Everywhere you would care to point a camera is amazing. I think this portion of the trail is one of the most naturally beautiful places on earth. It’s incredible and it’s the reason people spend so many hours on the trail. The path is bookended by two of the larger towns on the island but it feels isolated and completely separate from the experiences that the rest of Santorini offers. The only people I met on the hike were two local women who were digging up plants near a tiny chapel. There are no black, white, or red beaches. There’s no parade of donkeys. There are no cafes or bars. No ancient ruins, either. There’s barely anything except for a small monastery and the island itself and it’s wonderful.

I could see Finikia in the distance, and so I continued to walk toward it. As you get closer to Finikia, the trail finally starts going downhill and eventually joins up with the main road. There may be another path that avoids the road and stays on the cliffs, but after already taking two wrong turns that dead ended, I decided to take the more conventional route into town. By the time you get there, you’ll be glad to have smooth paved ground under your feet as you will have spent the last few hours alternating between dirt, gravel, and cobblestone paths. Once again, I cannot overstate the importance of comfortable shoes for the walk. At this point on my hike, I’d taken at least a hundred photos and could have easily taken more. The breadcrumb trail was extensive.

Finikia is the counterpart to Imerovigli. It has the amenities that were missing from the previous portion of the trail and eases you back into the more familiar setting of Oia. In the interest of full disclosure, I’d abandoned all thought of walking back to Fira by this point. I had a handful of Euros in my pocket, so I planned to take the bus back to Fira once I made it to Oia.

Once I got to Oia, I took time to get some lunch and rest a while. I explored the town the same way I did with Fira, by zigzagging through the streets and randomly climbing and descending stairs. I saw Amoudi Bay, but the 235 steps that led down to it were daunting and I wasn’t completely sure that I would be able to make it back up if I went down. After doing some exploring and checking out the northern coast of the island, I walked back to the town center and hopped the bus back to Fira. As we cruised down the eastern coast, I looked back at the ridge and realized just how far I’d gone… unintentionally.

In closing, if you didn’t have the patience to read the previous 1500 words, and just want a summary of the hike, here are the most important points:

Wear comfortable shoes, eat a big breakfast, take as many photos as you can, try not to trespass, carry bus fare and enjoy the views.